SEMINARIO QUÍMICA ORGÁNICA 30-6-25
EXPOSITOR: Lic. Josefina Huck
TÍTULO: "Iron-Catalyzed Enantioselective Multicomponent Cross-Couplings of α-Boryl Radicals".
FUENTE: Cassandra R. Youshaw, et al. Org. Lett. 2023, 25, 46,
8320–8325. https://doi.org/10.1021/acs.orglett.3c03387.
DÍA, HORA y LUGAR: Lunes 30 de junio de 2025, 14:00 h, Aula 18 y virtual.
Modalidad virtual, Link: meet.google.com/hjn-ygro-twf (Plataforma MEET GOOGLE)
Resumen: Despite recent interest in the development of iron-catalyzed transformations, methods that use iron-based catalysts capable of controlling the enantioselectivity in carbon–carbon cross-couplings are underdeveloped. Herein, we report a practical and simple protocol that uses commercially available and expensive iron salts in combination with chiral bisphosphine ligands to enable the regio- and enantioselective (up to 91:9) multicomponent cross-coupling of vinyl boronates, (fluoro)alkyl halides, and Grignard reagents. Preliminary mechanistic studies are consistent with rapid formation of an α-boryl radical followed by reversible radical addition to monoaryl bisphosphine-Fe(II) and subsequent enantioselective inner-sphere reductive elimination. From a broader perspective, this work provides a blueprint to develop asymmetric Fe-catalyzed multicomponent cross-couplings via the use of alkenes as linchpins to translocate alkyl radicals, modify their steric and electronic properties, and induce stereocontrol.
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